Massie has spent more than a decade cultivating a reputation as one of Congress’s most independent Republicans. A Tea Party libertarian, he frequently bucks both parties on spending and foreign policy and has emerged as one of the few GOP lawmakers willing to directly oppose Trump during his second term.

“I think it’s hard to get motivated to go vote for nobody against somebody, but I think it’s easier to be motivated to go vote for somebody you believe in. Like nobody really believes in my opponent,” Massie explained.

Massie has survived primary challenges before, but this race is his most difficult. Outside groups aligned with Trump have blanketed Kentucky airwaves with more than $25 million in ads boosting Gallrein and blasting Massie.

The incumbent has also faced scandal in the closing days of the race. An ex-girlfriend accused Massie of offering her $5,000 to drop a workplace wrongful termination complaint against his political ally, Rep. Victoria Spartz (R-IN). Massie has denied the allegations.

Polling in the race has been sparse, but it seems to suggest that Massie is in trouble. A Quantus Insights poll, conducted between May 11 and May 12, found Gallrein leading by 8 percentage points. The results showed a pronounced shift from April, when Quantus found Massie up by 9 percentage points.

When asked by the Washington Examiner if this has been his most difficult race yet, Massie responded, “I think it’s the most expensive in history, like anywhere.”

Massie was first elected to Congress in 2012. In that time, he’s always been an outspoken critic of how Washington has done business under both Republican and Democratic governance.

The independence appears to have especially infuriated Trump, who has often maintained a more flexible relationship with Republican dissent than even critics sometimes acknowledge.

While publicly emphasizing loyalty, Trump has frequently endorsed Republicans who disagreed with him politically or even criticized him personally. This cycle alone, Trump backed John Sununu for Senate in New Hampshire despite the candidate previously calling him a “loser” and endorsing Nikki Haley in the 2024 Republican primary.

Massie, however, appears to have crossed a different line. Unlike Republicans who criticize Trump rhetorically before eventually falling in line, Massie has repeatedly used his position in Congress to directly obstruct parts of Trump’s agenda.

This Congress alone, Massie opposed Trump’s signature tax cuts, teamed up with Democrats to release the Epstein files, and forced vote after vote on reining in the president’s power to conduct war on Iran.

“We got to get rid of this loser. This guy is bad,” Trump said during a visit to Massie’s district earlier this year. “He’s disloyal to the Republican Party, he’s disloyal to the people of Kentucky, and most importantly, he is disloyal to the United States of America.”

Despite Trump’s attacks, Massie has retained allies even among some of Trump’s biggest supporters on Capitol Hill.

“Below is my friend Thomas Massie. He loves America and is fighting to save it,” Rep. Lauren Boebert (R-CO) posted on X Friday with pictures of both men. “Also below is my friend and President, Donald Trump. He’s put his life on the line to save this great country. I support both of these men.”

LAUREN BOEBERT TO CAMPAIGN FOR THOMAS MASSIE AHEAD OF TOUGH PRIMARY

Boebert is traveling to Kentucky to campaign with Massie ahead of the primary. Her support underscores the complicated position conservatives find themselves in as the president targets one of the Right’s most independently minded lawmakers.

The outcome of the Kentucky primary is likely to reverberate far beyond the state. A Massie loss would further cement Trump’s dominance over the GOP, while a victory could offer a road map for anti-establishment conservatives willing to challenge the president.